Chatham Rentals
From $784 per night (USD)VRBO
WATER VIEW OF STETSON COVE! UPDATED HOME WITH SO MUCH TO OFFER!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Sparkling Updated Home With Lovely Views Of Stetson Cove * * * * See end of this description for information a ...
From $784 per night (USD)VRBO
From $6834 per night (USD)VRBO
Your Ultimate Vacation Destination!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
This is your ultimate vacation destination! Simply stunning, custom built home with a grand farmer's porch! Sit and sip ...
From $6834 per night (USD)VRBO
From $641 per night (USD)VRBO
Happy Yellow House - Family and pet-friendly; walkable to Ridgevale Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
*Note: The minimum stay dropped to 3 nights for Jan-March! Other months are still 7 nights as a minimum. The monthly dis ...
From $641 per night (USD)VRBO
From $769 per night (USD)Expedia
CHATHAM WATER FRONT/VIEW HOUSE FIRST TIME RENTAL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Perfect vacation spot. Enjoy your vacation on this 3 bedroom 2 bath, Central air conditioned house bordering Emery Lake ...
From $769 per night (USD)Expedia
From $1001 per night (USD)VRBO
Reuben Young House: Two 1st Floor King Master Suites. Close to Town & Beaches.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Charming circa 1820 antique newly renovated. close to downtown Chatham (1.5 miles). Close to Fish Pier, Ryders Cove, Oys ...
From $1001 per night (USD)VRBO
From $115 per night (USD)VRBO
Pleasant Forest Shores #1 S. Chatham: Classic Swedish ''Stuga'' style near beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
NOTE: Booking of EXISTING customers should begin on 02/01/25. New guests can ONLY apply for 2025 WAIT LIST at this time ...
From $115 per night (USD)VRBO
From $1099 per night (USD)VRBO
Family friendly luxury home with heated pool and spa
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Gorgeous home in Chatham with a brand new heated saltwater pool and hot tub. The open floor plan, combined living and ...
From $1099 per night (USD)VRBO
From $281 per night (USD)VRBO
Cozy one bedroom on White pond (Must bring your own linens)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
2 Person only. Charming little classic Cape cottage located close to town, beaches and bike trail. The cottage is nestl ...
From $281 per night (USD)VRBO
From $304 per night (USD)VRBO
Quaint 2 Bedroom Cottage Overlooking White Pond
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Must bring your own linens. Perfect getaway to relax and unwind. Located in a small 5 acre enclave of cottages nestled u ...
From $304 per night (USD)VRBO
From $385 per night (USD)Expedia
Solitude near the beach, High speed wifi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Comfort, convenience and beauty a mere 5 minute stroll away from Ridgevale beach. Nestled in a quiet neighborhood, our b ...
From $385 per night (USD)Expedia
From $454 per night (USD)VRBO
Large Yard, Quiet; 300 Yd on Sidewalk to Hardings Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
If you have small children or would just like some peace and serenity, Blue Skye is for you. Lots of lawn to run and pl ...
From $454 per night (USD)VRBO
From $945 per night (USD)VRBO
Location! Pool & Spa! 2 Primary Suites, Walk to Town, Beach, Chatham Bars Inn
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
**As is customary with Cape rentals, there is a cleaning fee and a 14.45% local and state lodging tax. Please enter desi ...
From $945 per night (USD)VRBO
From $497 per night (USD)VRBO
Pleasant Chatham Cape
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Pleasant Chatham Cape - A Classic Cape Cod Getaway with Modern Comforts Welcome to Pleasant Chatham Cape, a charming 4- ...
From $497 per night (USD)VRBO
From $1253 per night (USD)VRBO
Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This picture perfect Townhome is set on 17.5 acres on beautiful Oyster. Beautifully and meticulously designed, this Town ...
From $1253 per night (USD)VRBO
From $486 per night (USD)VRBO
Three Bedroom Updated Home -- Just Minutes to Pleasant Bay, Town and Bike Path!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sun Filled, Completely Renovated 3 Bedroom, 2 Bath. Minutes from Pleasant Bay or Downtown, Perfect for your Cape Adven ...
From $486 per night (USD)VRBO
From $824 per night (USD)VRBO
Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A charming 3 bedroom, 2.5 bath cape with large kitchen and private backyard, patio and deck that abuts conservation lan ...
From $824 per night (USD)VRBO
From $912 per night (USD)VRBO
Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
1.2 acres of beautiful waterfront property. Pond is great for canoes, fishing, and swimming. Canoe provided for tenant u ...
From $912 per night (USD)VRBO
From $1129 per night (USD)VRBO
FIVE BEDROOM-- WATERFRONT RETREAT ON RYDERS COVE, PERFECT SPOT TO KAYAK AND CANOE.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 13
Enjoy this Special Waterfront Retreat on Ryders Cove, a Perfect Spot to Kayak or Canoe! * * * * See end of thi ...
From $1129 per night (USD)VRBO
From $277 per night (USD)VRBO
Renovated cottage 1 mile to beach in Chatham!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Totally renovated bungalow style cottage with a sunny open floor plan, brand new appliances and furnishings on quiet str ...
From $277 per night (USD)VRBO
From $765 per night (USD)VRBO
FOUR BEDROOM IN TOWN LOCATION -- CLOSE TO OYSTER POND BEACH AREA.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Wonderful In Town Location with a Main House and One Bedroom Cottage. * * * * See end of this description for i ...
From $765 per night (USD)VRBO
From $353 per night (USD)VRBO
Idyllic Cape House Close to Beaches
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Idyllic cape house close to beaches and ponds, as well as walking distance to restaurants, bars, ice cream, and shops in ...
From $353 per night (USD)VRBO
From $865 per night (USD)VRBO
Chatham's Best Views-Harbor & Atlantic; On the Beach 4 Kayaks, 2 SUP's, 5 chairs
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
This exquisite ONE (1) family home, “Upside Down” house, easily compares favorably to ocean front suites at the Chatham ...
From $865 per night (USD)VRBO
From $596 per night (USD)VRBO
Centrally located home with patio, a/c included, walking distance from town.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Centrally located vacation home with central air conditioning in an ideal location with 3 bedrooms, 2 full baths plus ...
From $596 per night (USD)VRBO
From $968 per night (USD)VRBO
FIVE BEDROOM -- AMAZING WATER VIEWS OF NANTUCKET SOUND, MINUTES TO ASSOCIATION BEACH
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 11
Just 1/10 of a Mile to Deeded Association Beach with amazing water views of Nantucket Sound. * * * * See end of ...
From $968 per night (USD)VRBO
From $876 per night (USD)VRBO
Beautiful and Spacious, Sleeps 10 and a Quick Walk to Chatham's popular Harding's Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
RECENTLY REDUCED FOR ALL JUNE WEEKS! BOOK A LONG WEEKEND GETAWAY TODAY! Spacious Updated Home, Very Close to Popu ...
From $876 per night (USD)VRBO
From $347 per night (USD)Expedia
On Goose Pond Pet Friendly Wifi Water Views Private
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
1 Bedroom- 1 Bath- Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of ...
From $347 per night (USD)Expedia
From $236 per night (USD)VRBO
TWO BEDROOM PET FRIENDLY COTTAGE -- 1/4 MILE TO RIDGEVALE BEACH
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
For those that love the Beach! Just 1/4 mile to beautiful Ridgevale Beach. * * * * See end of this description ...
From $236 per night (USD)VRBO
From $1639 per night (USD)VRBO
Ocean views, path to beach, short walk to lighthouse and town, sleeps 12
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
This listing combines a large house having a deck with a beautiful view of the ocean and an adjacent cottage allowing fo ...
From $1639 per night (USD)VRBO
From $1042 per night (USD)VRBO
Perfect House to Enjoy Family & Friends!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Main house has 3 bedrooms 2 baths. Open floor plan is great for a big group. Apartment has a full kitchen, living area a ...
From $1042 per night (USD)VRBO
From $523 per night (USD)VRBO
Summer Hydrangea: Chatham's Truly Exceptional Summer Retreat
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Summer Hydrangea, quite possibly the finest property value for an exceptional summer rental in Chatham. Priva ...
From $523 per night (USD)VRBO
From $412 per night (USD)VRBO
Pondfront cottage on Stillwater Pond
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Set your clocks back 50 years, and fish for your breakfast from your own dock or row-boat. This setting has been descri ...
From $412 per night (USD)VRBO
From $681 per night (USD)Expedia
Walk to Private Beach Hot Tub AC Water Views The Sea Mist
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3 Bedroom - 2 Baths - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $681 per night (USD)Expedia
From $477 per night (USD)VRBO
Near Beach, AC, WiFi, Pet friendly, fenced yard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedrooms- 2 Bathrooms- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
From $477 per night (USD)VRBO
From $2043 per night (USD)VRBO
Chatham's Best Location / Oceanside / Walk to Town and Beaches
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
This exquisitely furnished, charming Cape Cod house is within an easy walk of Chatham's beaches, Fish Pier, Lighthouse, ...
From $2043 per night (USD)VRBO
From $950 per night (USD)VRBO
AC, Pool, Hot Tub, Fenced Yard, Beach vacation home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious four bedroom, two bathroom, single family home with central air, above ground pool, hot tub, fire pit, and fenc ...
From $950 per night (USD)VRBO
From $1191 per night (USD)Expedia
Sail Loft: 489-C Updated Chatham Family Compound, Heated Pool w/Hot Tub, Walk to Town/Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This property is professionally managed by Pretty Picky Properties Updated Chatham Family Compound, Heated Pool with Ho ...
From $1191 per night (USD)Expedia
From $818 per night (USD)VRBO
SHORT WALK TO LIGHTHOUSE BEACH AND TOWN....WATERFRONT ON MILLPOND WITH PATH TO WATER!!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Fabulous Old Village Location, Minutes to Lighthouse Beach and Town * * * * See end of this description for inf ...
From $818 per night (USD)VRBO
From $373 per night (USD)VRBO
SHORT WALK TO LIGHTHOUSE BEACH, ANDREW HARDINGS LANE BEACH AND TOWN!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Close to Town, Lighthouse Beach and Andrew Hardings Lane -- Desirable Old Village Location! * * * * See end of ...
From $373 per night (USD)VRBO
From $416 per night (USD)VRBO
Peaceful, Charming, Quiet, Airy, Cozy - Take A Look!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This 3 bedroom 2 bathroom two-story cape is private, quiet, and overlooks a lovely cranberry bog. Inside it's airy and o ...
From $416 per night (USD)VRBO
From $777 per night (USD)Expedia
Sand Dunes and Salty Air - 5 minutes drive to beaches!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A beautiful house on a quiet cul-de-sac that is close to everything that Chatham has to offer. It is less than 2 miles f ...
From $777 per night (USD)Expedia
From $4904 per night (USD)VRBO
Sweeping Ocean Views, Gorgeous Home With Guest Cottage, Pool and Tennis Court
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
This cherished family home + guest cottage in coveted section of North Chatham is available for only one or two weeks e ...
From $4904 per night (USD)VRBO
From $650 per night (USD)VRBO
Ocean & Marina Views From This Charming Cottage! Walk To Beach & Town.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Charming cottage right next to Outermost Marina with views of the boats & water. The quintessential beach house! If you ...
From $650 per night (USD)VRBO
From $429 per night (USD)VRBO
Three Bedroom Updated Property -- Short Walk to Forest Beach and Pleasant Street Beach.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful home that is 2/10's mile to Forest Beach and 3/10's mile to Pleasant Street Beach - Both Nantucket Sound beach ...
From $429 per night (USD)VRBO
From $607 per night (USD)VRBO
Beautiful Cape Cod Gem
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
This classic Cape Cod house is full of traditional charm and features without skimping on the modern amenities. Upstair ...
From $607 per night (USD)VRBO
From $342 per night (USD)VRBO
South Chatham, Ma. 02659. Seasonal Cottage, Walk to Pleasant Street Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Cottage has been in family for over 40 years but updated over the years. Seasonal beach cottage 1 full bath, king bedro ...
From $342 per night (USD)VRBO
From $507 per night (USD)VRBO
Sea views steps to Ridgevale Beach - Airy Cottage. Modern Amenities. Pet.linen
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Pet ok with approval first. Bright and airy cottage sleeps max 5 (2 BR - 1Q, 2T) plus single pull out sofa bed in hi liv ...
From $507 per night (USD)VRBO
From $550 per night (USD)VRBO
Lover's Lake Escape - Chatham Lakefront home with private access to Lover's Lake
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This home is represented by Nauset Rental, a local vacation rental management company. Enjoy the serenity of Lover's L ...
From $550 per night (USD)VRBO
From $1018 per night (USD)Expedia
North Chatham Waterfront Oasis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Amazing views! Enjoy the views of Pleasant Bay out to the ocean and the Outer Beach! This 4 bedroom 3 bath home is spaci ...
From $1018 per night (USD)Expedia
From $813 per night (USD)VRBO
Walk to Pleasant Street Beach, Renovated, Central AC, King Bed!!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Cape Charmed Chatham Colonial! Nearby to Pleasant Street Beach! This newly remodeled, bright and beautifully decorated, ...
From $813 per night (USD)VRBO
From $378 per night (USD)VRBO
Walk to Ridgevale Beach in 7 minutes, Central Air, Beautiful yard Fast Internet
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Adorable Chatham Ridgevale Beach House With Beautiful Gardens! *******7 night minimum stay Saturday to Saturday***** ...
From $378 per night (USD)VRBO
From $2029 per night (USD)VRBO
Walk to Beach Heated Pool Pet Friendly AC WiFi Sand Simeon
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
6 bedrooms- 6.5 Bathrooms- Sleeps 14 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. ...
From $2029 per night (USD)VRBO
From $506 per night (USD)Expedia
Walk to Beach, Central AC, WiFi, great outdoor space
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedroom- 3.5 Bathrooms- Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. ...
From $506 per night (USD)Expedia
From $1937 per night (USD)VRBO
In Town Location Near Beach Pet Friendly Sleeps 18
- Bedrooms:
- 5
- Bathrooms:
- 8
- Sleeps:
- 18
8 Bedrooms- 5.5 Bathrooms- Sleeps 18 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. ...
From $1937 per night (USD)VRBO
From $809 per night (USD)Expedia
Walk to Beach, AC, WiFi, Private, Fire pit, Dogs Welcome
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
4 Bedroom- 3 Bathroom- Sleeps 9 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $809 per night (USD)Expedia
From $317 per night (USD)VRBO
Near Beach, Renovated Condo, AC, Wifi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
1 Bedroom- 1 Bathroom- Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $317 per night (USD)VRBO
From $665 per night (USD)Expedia
Lake front, Near Beach, AC, WiFi, Pet Friendly near Bike Path
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedroom - 2.5 Baths - Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $665 per night (USD)Expedia
From $532 per night (USD)VRBO
Walk to Beach Central AC WiFi Private The Rosa Rugosa
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3 Bedroom - 2 Baths - Sleeps 6 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $532 per night (USD)VRBO
From $749 per night (USD)Expedia
Close to Beach and Town Pet Friendly A C The Cape House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedrooms- 2 Bathrooms- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
From $749 per night (USD)Expedia
From $601 per night (USD)VRBO
Walk to Beach Quarter Mile to Bike Trail AC Wifi Summer Oasis
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
3 Bedroom - 2.5 Baths - Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Man ...
From $601 per night (USD)VRBO
From $1459 per night (USD)Expedia
Walk to Beach and Town, Hot tub, Sleeps 8, Pet Friendly
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedroom (2 Primary) - Loft - 5.5 Bathroom - Sleeps 8 During Peak Summer Season Until Labor Day - a 7-night Friday-to-F ...
From $1459 per night (USD)Expedia
From $742 per night (USD)VRBO
Ocean views Walk to Beach Pet Friendly AC Private
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
4 Bedroom - 4 Baths - Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. This ...
From $742 per night (USD)VRBO
From $923 per night (USD)Expedia
Town Home Community pool tennis AC
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
2 Bedroom - 3 Bathroom - Accommodates 6 Comfortably During peak summer weeks it is typical for our properties to require ...
From $923 per night (USD)Expedia
From $472 per night (USD)VRBO
Walk to Beach, Pet Friendly, AC units, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
4 Bedroom- 2 Bathroom- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $472 per night (USD)VRBO
From $449 per night (USD)Expedia
Near Beach Close to Town AC Units WiFi BreakAway
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedroom-3 Bathroom- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $449 per night (USD)Expedia
From $2538 per night (USD)VRBO
Walk to Beach, Heated pool, AC, WiFi, modern coastal decor, dog friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
4 Bedroom - 3.5 Baths - Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
From $2538 per night (USD)VRBO
From $469 per night (USD)Expedia
Walk to beach, AC, Gourmet Kitchen, Family friendly ranch, Sea Glass
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
3 bedroom- 2 bath- sleeps 7 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many of ...
From $469 per night (USD)Expedia
From $932 per night (USD)VRBO
Charming Waterfront House in Chatham
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Very private lakefront setting with spectacular views and private beach. Filled with Charm. It was the original Ice Hous ...
From $932 per night (USD)VRBO
From $418 per night (USD)Expedia
Walk to Beach Central AC WiFi Beach Pearl
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
2 bedrooms- 2 baths- sleeps 5 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many o ...
From $418 per night (USD)Expedia
From $735 per night (USD)VRBO
FOUR BEDROOM-- CLOSE TO TOWN AND TWO SALTWATER BEACH AREAS!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy The Loop from this spectacular rental property-- a beautiful two mile walking path boasting spectacular ocean view ...
From $735 per night (USD)VRBO
From $963 per night (USD)VRBO
Charming , very private 4 bedroom, 3.5 Bath Cape. Walk to Town & Oyster Pond
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
A charming 4 bedroom, 3.5 bath cape with large kitchen, private backyard, includes all amenities, patio and deck that ...
From $963 per night (USD)VRBO
From $1316 per night (USD)VRBO
AWESOME LOCATION 200 YDS TO CHATHAM VILLAGE & BEACH WITH GREAT WATER VIEWS
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 13
Location ! Location! Location ! Everything within walking distance . . . 200 yards to Chatham downtown, 200 yards to pub ...
From $1316 per night (USD)VRBO
From $536 per night (USD)VRBO
3 bed 3 bath. Premium linens provided. Pet friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
When you arrive you will find that our architect maximized light, air and views, with great flow from the upstairs vault ...
From $536 per night (USD)VRBO
From $210 per night (USD)VRBO
Delightful Cottage for Two
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This true Cape Cod cottage is ideal for a couple. Located in a 6 acre private community on beautiful White Pond. It is n ...
From $210 per night (USD)VRBO
From $944 per night (USD)VRBO
Chatham rental, 4 bed 3ba ~ walk to the beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
WALK TO JACKKNIFE COVE BEACH in Chatham from this charming, clean, and well-kept home. Enjoy s'mores with the kids at ou ...
From $944 per night (USD)VRBO
From $384 per night (USD)VRBO
Charming Cape Cottage in Chatham, 2 Min From Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Forest Sands cottage is comfortably decorated in Classic Cape style, a 2 minute walk from Forest Beach, and 10 minute sp ...
From $384 per night (USD)VRBO
From $1931 per night (USD)VRBO
Luxury 9 BR Home with Heated Pool in Downtown Chatham
- Bedrooms:
- 10
- Bathrooms:
- 9
- Sleeps:
- 21
This wonderfully renovated 1877 home, nestled in downtown Chatham, is centrally located within walking distance from eve ...
From $1931 per night (USD)VRBO
From $2912 per night (USD)VRBO
Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.\n
- Bedrooms:
- 5
- Bathrooms:
- 8
- Sleeps:
- 18
New heated gunite pool. 18X40 with automatic pool cover, and completely fenced in for safety. Design includes many plant ...
From $2912 per night (USD)VRBO
From $306 per night (USD)VRBO
Walk to School House Pond in Chatham.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This 2500sq ft house is 8yrs old and offers all the toys including a hot tub, sauna, bikes and kayaks for guest use. Fro ...
From $306 per night (USD)VRBO
From $389 per night (USD)VRBO
Fully Renovated Chatham 3 Bedroom with Water Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This home is represented by Nauset Rental, a local vacation rental management company. Beautiful recently renovated Ch ...
From $389 per night (USD)VRBO
From $943 per night (USD)Expedia
Sprawling Family home located across from Chatham Harbor
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Sprawling Family home 3-minute walk to the beautiful Chatham Beach Relax and enjoy your summer family vacation in this ...
From $943 per night (USD)Expedia
From $465 per night (USD)VRBO
Spacious, private cottage just a few minutes walk to Ridgevale Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summer living less than a 1/2 mile from one of Cape Cod's best beaches! This home offers room to spread out, with living ...
From $465 per night (USD)VRBO
From $355 per night (USD)VRBO
Secluded Chatham Cottage Near Hardings Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our renovated 'old Cape' style cottage, with a sunny, open floor plan, brand new appliances and furnishings, ...
From $355 per night (USD)VRBO
From $302 per night (USD)VRBO
Near Harding's Beach, 4 min walk to Oyster River. 3BR, 2Bath, enclosed deck area
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Just off of Barnhill Rd on the way to popular Harding's Beach, this air conditioned, updated three bedroom house off ...
From $302 per night (USD)VRBO
From $525 per night (USD)VRBO
Location Location! Perfect 2-Bedroom Condo On Main Street In Chatham
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Pet Friendly! Two bedroom luxury vacation condo on second floor of home in the heart of Chatham Village! Head up the sta ...
From $525 per night (USD)VRBO
From $1278 per night (USD)VRBO
SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the SeaGlass House! Charming and bright, open concept Cape house perfect for creating long lasting memories. ...
From $1278 per night (USD)VRBO
From $1654 per night (USD)VRBO
Beachfront Nantucket style home with amazing views on 3 acre estate setting
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 9
'The Bluff House' is a very private turn of the century informal home located down a private country lane directly on th ...
From $1654 per night (USD)VRBO
From $358 per night (USD)VRBO
Lovely Chatham Home Near the Bike Trail (1524)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy this contemporary Chatham home comfortably accommodating 6 just minutes from the Cape Cod Rail Trail, for great cy ...
From $358 per night (USD)VRBO
From $506 per night (USD)Expedia
Beautifully Maintained 3BR Colonial Close to Forest Beach (1577)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
***NEW FOR 2025-all new hard wood flooring through the house!*** This comfortable rustic home has 3 bedroom, 2 bath, a ...
From $506 per night (USD)Expedia
Click For PricingVRBO
Stylish Cape in North Chatham ~ Walk to Private Neighborhood Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful cape in upscale Harbor Cove neighborhood. Recently renovated with all new furnishings and appliances. 4 BRs, 2 ...
Click For PricingVRBO
From $629 per night (USD)VRBO
Beautiful Home In Chatham, MA. Private Pool. 2 Min Walk to Town, 8 to Beach! A/C
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Spend your Chatham vacation at the POOL! This wonderful home is just minutes to everything downtown Chatham has to offer ...
From $629 per night (USD)VRBO
From $358 per night (USD)VRBO
Pet friendly home with central air (1998)
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This adorable PET FRIENDLY cape style home is located on a peaceful, residential, dead end road, close to two fresh wate ...
From $358 per night (USD)VRBO
From $372 per night (USD)VRBO
Charming Chatham Beach House; Walk to Hardings Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
You will love Rhododendron House -- a recently updated 2 bedroom vacation house. This private hilltop retreat is located ...
From $372 per night (USD)VRBO
From $325 per night (USD)VRBO
Cute Cottage - Half Mile to Nantucket Sound! (1976)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This cottage is perfect for a relaxing vacation. It is located in a quiet location in South Chatham, only ½ mile to Nant ...
From $325 per night (USD)VRBO
From $322 per night (USD)VRBO
Cozy renovated classic Cape cottage a short walk to Forest Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This cute 2 bedroom 1 bath cottage was recently completely renovated inside and is bright, clean and cozy. It is locat ...
From $322 per night (USD)VRBO
From $2615 per night (USD)VRBO
Exquisite Old Cape Charm, Spectacular Views, Huge Private Beach, Sleeps 20
- Bedrooms:
- 6
- Bathrooms:
- 13
- Sleeps:
- 20
This is the old Cape Cod at its loveliest and most peaceful. Although the oldest part of the house was originally a cott ...
From $2615 per night (USD)VRBO
From $306 per night (USD)Expedia
Cape Cod Chatham Water View Retreat
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Secluded Cape Cod Chatham retreat on tidal estuary creek. Conservation land assures privacy. Easy and safe private entra ...
From $306 per night (USD)Expedia
From $211 per night (USD)VRBO
Chatham Cottage on the Big Pond One Mile to Ocean Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Get away and relax at our cottage on White Pond in beautiful Chatham Cape Cod. The cottage has a private fresh water bea ...
From $211 per night (USD)VRBO
From $358 per night (USD)VRBO
Carriage House with Beautiful Water View, Steps to Beach & Main Street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located overlooking Chatham's beautiful Oyster Pond, this two bedroom carriage house is the perfect location for your Ca ...
From $358 per night (USD)VRBO
From $335 per night (USD)VRBO
THREE BEDROOM UPDATED HOME--CLOSE TO FISH PIER AND TOWN.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Cute Chatham Getaway - Just 6/10's of a Mile to Chatham Fish Pier and 8/10's of a mile into Town center. * * * * ...
From $335 per night (USD)VRBO
From $318 per night (USD)VRBO
Stay in a Chatham Windmill! Beautiful Water View, Steps to Beach & Main Street
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
NEWLY RENOVATED CHATHAM WINDMILL for your special Cape Cod vacation experience! Located overlooking Chatham's beautiful ...
From $318 per night (USD)VRBO